Great Lakes Luxury Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Luxury vacation packages in Great Lakes
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥391,422, price is now ￥353,505 per person
￥353,505
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Everything was great! Except I must say the area was not as safe as it use to be!
Reviewed on Apr 1, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥635,786, price is now ￥516,592 per person
￥516,592
per person
May 27 - Jun 1
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was ￥473,838, price is now ￥423,654 per person
￥423,654
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.2/10 Wonderful! (2,858 reviews)
Very nice hotel with an amazing, historical swimming pool. The location is perfect to do the tourist things!
Reviewed on Mar 31, 2026
5* Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥635,786, price is now ￥516,592 per person
￥516,592
per person
May 27 - Jun 1
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
Shangri-La Toronto
Downtown Toronto
Price was ￥632,645, price is now ￥585,497 per person
￥585,497
per person
Jun 14 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Toronto (YYZ)
9.6/10 Exceptional! (1,199 reviews)
Easy and pleasant check in as usual! The rooms are great and they treat my dog very well. Always high quality service.
Reviewed on Apr 1, 2026
The St. Regis Toronto
Downtown Toronto
Price was ￥722,372, price is now ￥671,033 per person
￥671,033
per person
Jun 18 - Jun 23
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Toronto (YYZ)
9.4/10 Exceptional! (1,005 reviews)
Excellent service, great location, comfortable bed
Reviewed on Mar 17, 2026
3 Night Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was ￥473,838, price is now ￥423,654 per person
￥423,654
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.2/10 Wonderful! (2,858 reviews)
Very nice hotel with an amazing, historical swimming pool. The location is perfect to do the tourist things!
Reviewed on Mar 31, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥440,914, price is now ￥400,753 per person
￥400,753
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Everything was great! Except I must say the area was not as safe as it use to be!
Reviewed on Apr 1, 2026
4 Night Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥398,698, price is now ￥352,473 per person
￥352,473
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥512,798, price is now ￥416,836 per person
￥416,836
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
Top Luxury Great Lakes Hotels
The Omni King Edward Hotel
37 King St E Toronto ON
Discover luxurious lodging at The Omni King Edward Hotel, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe amenities ...
9.6/10 Exceptional! (2,492 reviews)
Excellent stay!
Reviewed on Apr 1, 2026
Fairmont Royal York
100 Front St West Toronto ON
Treat yourself to a luxury stay at Fairmont Royal York, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The 3 bars, indoor ...
9/10 Wonderful! (7,821 reviews)
Clean room great staff
Reviewed on Apr 1, 2026
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Trump International Hotel & Tower Chicago is a lush 5-star boutique property where you can be treated to deep soaking bathtubs and pillowtop beds. The spa, indoor ...
9.4/10 Exceptional! (1,848 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
